


Plan B for Buttsex

by brethilaki



Category: Supernatural
Genre: Bottom Castiel, Car Sex, Episode: s05e03 Free to Be You and Me, First Time, M/M, PWP, Season/Series 05, Top Dean
Language: English
Status: Completed
Published: 2013-01-22
Updated: 2013-01-22
Packaged: 2017-11-26 10:34:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,972
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/649627
Author URL: https://archiveofourown.org/users/brethilaki/pseuds/brethilaki
Summary: <blockquote class="userstuff">
              <p>Set in Season 5 Episode 3 "Free to Be You and Me" - aka The One Where Dean Takes Cas to a Whorehouse and Promises Him Sex, except in this version, Dean is somewhat more drunk actually delivers.</p>
            </blockquote>





	Plan B for Buttsex

Phase 1

 

“I haven't laughed that hard in years,” Dean realized as he dragged his doomed angel out of the back door of the strip joint, having more fun than he would be willing to admit. Various thoughts of variable clarity blurred together in his mind (muddied by drink and stirred by adrenaline), but the sharpest was a promise and a sense of purpose put in focus by the red lens of sex.

He had given his word Cas wouldn't die a virgin. It wasn't often he invoked Bert and Ernie's sexuality as a measure of his surety, and it wasn't an oath to be broken lightly.

The heat in Dean's belly agreed. Surely it would be an affront to his honor as a man to prove his promises so idle.

“Oh, well,” Dean thought aloud as he opened back door of the Impala and threw a shocked Castiel into the rear seat, crawling in on top of him and pushing him back till his head bumped the window of the opposite door whence it stared up at Dean in desperate confusion, “time for plan B...”

“Dean?” The edge to the angel's voice could have been panic or concern.

“Yeah, normally I don't do virgins,” Dean offered by way of explanation, considering before he added, “or dudes. But I made a promise to you, Cas, and I am a man of my word.” He gave a winning grin and Cas frowned back and swallowed. There was confusion still in his upturned eyes, but they had lost the edge of horror that had contorted them back in the “den of antiquaries” (“inquiries?” “soliloquys?” Dean felt like he was getting farther from the mark, so he dropped the thought).

“Dean...” Recognizing through impairment of his mind that Cas might actually be trying to say something, Dean waited this time for him to continue, but became impatient after several seconds of silence and soul-searching eyes.

“And I swear to God if you say anything about my father—”

“Dean, why?”

“Why? Why what? I already told you—” he ran a hand down the angel's spine and was rewarded with a shudder— “besides. I could ask you the same thing. You put your life on the line for me—repeatedly. You trust me—against your better judgment. You _like me_ , Cas.” It wasn't a question, but there was not quite enough confidence for it to be a statement. So Castiel paused, with parted lips, before deciding to confirm.

“Yes,” he said softly, but firmly, because it was the only thing he was entirely sure of at the moment. Dean stared like he hadn't actually been expecting Cas to agree, so the angel licked his lips and continued haltingly, the edge behind his monotone now unmistakeably nerves.

“Dean. You... say many things I do not understand, but your unwavering spirit makes you hard to doubt. I have met no angel, mortal, or demon so persistently willful in the face of such odds or persuasively self-assured in spite of such secret doubt. The truth is, Dean Winchester, I am... in awe of you.” Cas confessed quietly.

Dean stared harder, and Cas looked away, shifting uncomfortably. He tried to think of something to say to break the silence, but Dean's lips beat the words to his mouth.

Cas tensed. And froze. So Dean rubbed comforting circles into his arms and back and pressed soft kisses into his dry lips until he started to relax. And kiss back. Dean sucked and nipped at Cas's bottom lip. He nudged at the opening of Cas's lips with his tongue. Cas, completely out of his element, copied Dean's moves, but did seem to be able to take cues. So after a couple of unsuccessful tries at breaching chapped lips with his tongue, Dean pulled back, receiving a sigh of disappointment.

“Cas. Open your mouth.”

“What—”

“Just follow my lead.” said Dean, dipping his tongue between the parted lips before they closed. He was getting painfully frustrated (and this was the reason he preferred partners with experience), but he had to do right by Cas. It was least he could do to thank him for... well, everything. Literally.

And Cas followed his lead. He was inexpert but eager with his tongue, and to Dean's credit he let him ravage his mouth for a full second before losing patience and taking control. Cas became pliant, and he used the opportunity to begin removing the angel's clothes.

By the time he broke the kiss and started biting down the jaw and neckline, Castiel's upper half was down to a half-unbuttoned shirt. Dean peeled it off his chest and suckled a nipple, making Cas groan and shiver beneath him and tug needily at Dean's hair. Dean pulled back again to remove his own shirt and was met with a sight that made his hair stand on end: pale skin plated in silver light and embedded with ivory where shadow blocked the moon, a thing beauty with a halo of dark, tousled hair, but half destroyed like the ruins of Sodom Gomorrah consumed by fire and swirls of red sand. Cas panted shallowly and tried to pull him back down.

“Dean... I... I think I begin to understand the human fascination with sex.... this is very... good...” the words were slightly slurred and the thoughts slow-forming and disjointed. Dean laughed out loud.

“Cas, man, this... we haven't really made it to the sex part yet; Cas, this hardly counts as foreplay.”

“Of course,” Cas emended quickly. “I used the word broadly. Sex requires penetration.”

“Yeah, I don't know about that one,” Dean trailed a finger down Cas's chest slowly, not really thinking about what he was saying. He dipped the finger below the waistline of Cas's pants before pulling out to unbutton and remove them. “Maybe next time.”

“...Dean.” Oh, yeah.

“Oh, come on, Cas. After all you just said? After all this?” He rubbed Cas's half-hard cock through the fabric of his underwear, causing his hips to buck up and his head to slam back against the car door, wide blown eyes taking in the ceiling without actually seeing anything. “You're still going ahead with your little suicide mission? I don't understand you.”

“THIS—” Cas began on a sudden exhalation of surprise and pleasure, then paused to breathe before continuing. “This is exactly _why_ I'm doing it, Dean,” he gasped out at length in a strained voice, because Dean was palming his cock. “To save you. All for you.” The final words dissolved into a groan and one of Cas's hands flitted uncertainly and without guidance around Dean's, desperate for they seemed not to know what, and leaving Dean endlessly amused at his righteous ignorance. Having paused in his ministrations to give Cas the chance to speak, Dean started rubbing again, and Cas whimpered pathetically, clawing at his back.

“I'm not going to let you die tomorrow, Cas. You'll see,” Dean promised, not allowing himself the luxury of doubt. He freed Cas's cock and earned an relieved sigh, but his advantage of experience was limited here, and his own body was crying out for attention. Cas, given some reprise by Dean's sudden hesitation, became lucid enough to notice that much.

“Dean...” he whispered breathlessly, pawing deliciously at Dean's crotch. “I want to reciprocate.” He touched his own erection still resting in Dean's palm. “Please—” he plunged his hand below Dean's waistline and grasped experimentally at the bulge, twisting in imitation of Dean's movements and earning the approbation of a moan. “Is this right? Please, tell me what to do.”

Dean was out of his pants before Castiel finished the question. Twining his fingers in the hand Cas had left fisted unsurely around his dick, Dean guided Cas's thumb over the slit and shuddered against the touch. Castiel watched with fascination and intense concentration, monitoring Dean's face as he memorized the movement of his hands and the twitches and contortions they produced.

“Oh, God,” Dean sighed, and Castiel furrowed his brow but didn't complain.

With effort Dean pulled Cas's hand gently away from his cock and then, with only a small smile for warning, pressed their erections together, causing Cas's control to spiral away again and melt into a pool of pleasure and warmth around his groin. Dean replaced Cas's hand.

“Keep going, babe. You're doing great.”

Cas tried to concentrate like he had when he had only been pleasuring Dean, but it was hard when the man was kissing and touching all over his body, dividing his focus and making him forget to move. He finally gave up when Dean started rutting against him and, thrusting back, Cas discovered how much more mindless and natural this was. Dean's hands took over the stroking and Castiel's lost themselves in Dean's hair. There was a pressure building behind the pleasure. He wanted nothing more than to release it, but knew when he did, this would end.

“Dean...”

“Cas,” Dean moaned in response.

“Dean, I feel... I believe I am nearing orgasm. Don't want it to end...” he finished with a sharp gasp.

“Listen, you just live through tomorrow and we can do this again whenever the hell you want,” Dean panted. Cas's eyes fell closed and his head lulled back. His hips moved with Dean's, and his shoulders began moving with his hips, rubbing his back against the door of the car. Dean chuckled.

“What are you—”

“Touch me, Dean.”

“Heh. Cas, I am touch—”

“My back, Dean, touch my back!” Cas arched away from the door, peering at Dean pleadingly through narrow slits.

“Your back? Touch—?”

“My wings,” Cas finished the sentence for him. Dean reached around and rubbed Cas's shoulder blades. He didn't feel anything there... but Cas apparently did, because he sunk into the touch, letting his head fall to Dean's shoulder and gripping desperately at Dean's bare skin. He grazed his hand print, and Dean's nerves sang. Cas began trembling uncontrollably.

“It's coming... Dean... something is coming.”

“I know. Shhh. Let it out.” Dean stroked Cas's back soothingly until he came with a wail that could have pushed Dean over the edge, but he curled his toes and bit it back, stroking Cas through his orgasm first before he let himself go.

Spent, Dean let himself collapse onto his recovering angel, sticky-slick semen smearing between them. Cas's arms wrapped around his back and held him tight, making him feel safe in recollection of some dark unconscious time that must have been his ascent from Hell. He was about to slip into the unconsciousness of that memory when a quiet voice roused him,

“Dean.”

“Five more minutes.”

“Dean. Dawn is near. We need to go.”

“Do we have to?”

“Do you want to be Micheal’s vessel?”

“...no.”

“Then, yes. We have to.”

Dean pried himself reluctantly from the angel's chest and crawled gracelessly and still mostly naked into the driver's seat. Cas smiled fondly and mojoed his clothes back in order.

“You better not die, you son of a bitch,” Dean warned, starting the car.

“I can't,” Cas reminded him. “You won't let me.”

 

Phase 2

 

They left Raphael trapped in the house, buzzing with endorphins that put a spring their steps. So Dean wasn't really surprised when Cas pushed him up against the side of his baby and made a show of everything he had learned about lips and tongues the night before. Dean smiled into the kiss, groping casually at Cas's ass.

“I—my vessel—is erect—I can't stop it,” Cas punctuated his words with nips and licks.

“Yeah, excitement will do that to a man.” (Or, more normally, to a teenage boy, he thought).

“Dean, I think now... I think I want to experience penetration.” There was something very arousing about Cas's straightforward, unaffected language. Dean felt his dick twitch.

“You mean you want... uh... do you want to experience _penetrating_ or _being penetrated_...?” Dean felt like a dork talking about sex that way, but he didn't want to confuse Cas.

Cas considered.

“Which is better?”

“Dude, I don't know! I never—”

“I want to do what you want to do,” Cas cut in. Dean licked his lips.

“Okay. Yeah, alright, but if we're doing this, we're doing it in a bed...” Dean walked to the driver's seat of the car, mind flicking through motels he had noticed in the area and trying to sort them by apparent cleanliness, “and I might have to pick up—” Dean felt Cas's fingers on the back of his head “—a few things on the _what the..._ ” and the scenery dissolved into a dark room.

“Cas what the hell!” Dean swirled around. “My car—!”

“Dean...” Cas was whining, pleading, “please. I couldn't wait, it—it hurts...” he looked down. Dean followed his eyes then raised an eyebrow, bemused.

“Yeah, I'll bet...” he helped Cas free his erection from the now painfully tight suit pants, and Cas gasped and shivered.

“Wow. You really have _no_ self-control, Cas.” He received an irritated glare that might have been indignant if there were any dignity left in a man whose eyes were pleading and his pants slipping down his thighs.

“Alright. Okay. But if you want to... do what you want to do, we're going to need some lube.”

“Where does one find lube?”

“Supermarkets, sex shops... _hey_! Cas, your pants are still...! Dammit.” Cas reappeared after a few moments with a tube of “Gas and Go” brand anal lubricant and shoved it impatiently into Dean's hands.

“Dude! Did you just rob a seedy gas station with your dick hanging out?”

“Nobody saw me,” Cas insisted, pulling at Dean's shirt.

“Alright, slow down there... tiger,” Dean let his shocked disbelief fade into vague amusement. “Don't get too worked up, if you want this to last...” Dean pushed him onto the bed, stripping off clothes as they descended and trying not to be too curious about exactly where it was that Cas had taken them. Cas was still eager and energetic as a teenager, but Dean tongue-fucked his mouth into slack submission, reining the rest of his hypersensitive body firmly into his control.

“Relax, Cas,” he massaged his shoulder blades, then gently turned him onto his stomach and kissed them tenderly until Cas became limp and malleable beneath him. Dean ran a finger down the cleft of Cas's ass, causing a brief spasm of tension that faded when the finger withdrew.

“It's okay,” Dean whispered into his spine. “I've got to open you up, Cas, just keep your focus up here and relax.”

He drug his teeth lightly over the spot for emphasis, then began massaging it again with his lips and tongue as he lubed up a finger, found Cas's hole, and pushed slowly in.

“That is uncomfortable,” Cas complained with a whimper, “and painful.”

“It'll get better, Cas, I promise. Just don't think about it. Stay up here with me.” He nipped at Cas's upper back, waiting for Cas to adjust, then moved his finger a little, pushing deeper, crooking inward. Dean continued this way, stretching Cas slowly open with surprising patience until he found Cas's prostate and the angel became restless again.

“Dean... my control is dissipating. You should penetrate me before I orgasm. Please. Dean.” Dean decided with some pride that this counted as begging, and regretted he couldn't find the control himself to drag it out.

Instead he buried himself in a single stroke—better all at once, like taking off a band-aid, he justified to himself. He started rocking into the tight heat almost immediately in gentle, shallow thrusts, waiting for Cas to start moving with him before he increased his force and his pace. Cas moaned incoherently.

“Jesus, Cas... you're so tight...” Dean rested his forehead on Cas's back and relished his weak little cries and occasional attempts at forming his name until, overcome with a sudden need to see the face that could produce such broken sounds, he flipped the writhing mess of angel onto his back and hooked his legs over his shoulders, looking down into clouded eyes as he took hold of Cas's leaking cock. Dean had unraveled Cas; he deserved to enjoy the fruits of his labor. He watched the eyes go from dark to white as the dilated pupils rolled up under the hoods of Cas's heavy eyelids, his hands clawing helplessly at the sheets. Dean teased Cas's cock with a featherlight touch, watching him buck up, arch and contort his upper body in pleasure, part his lips in a silent plea. Dean was close himself. His thrusts were growing rougher and less measured, pushing Cas back along the bed until his head knocked softly against the wall.

So Dean got him off with a couple of more solid strokes before coming hard into the clenching muscle of his hole. His head rang with aftershock—unless that was Cas gasping curses in Enochian, which in fact it must have been, and the gasping was a broken and biblical Greek, the guttural moans Hebrew and Aramaic and the sonorous ones classical Arabic; and the snatches of intelligible speech were Latin, except when they were simply Dean's name.

Finally, Cas quieted looked up at him, dazed, as if he had just woken form a dream. There were still connected. Dean smiled down, trying not to analyze the feelings that were pumping through the blood still pounding in his ears. Instead he let himself fall and drift into an exhausted sleep—and this time Cas let him, too, watched him rest, safe, until the wee hours. Dean woke up alone in the back of his car, but there was a tingling in the hand-shaped scar on his shoulder that matched the tingling in the pit of his stomach, and he felt unaccountably good and hopeful, for the first time since he was five.


End file.
